The east end of Long Island has always invited a choice: wine country or ocean beaches, quiet harbors or destination dining. We say skip the choice. With a thoughtful route and a few ferry crossings, a long weekend is enough to experience both sides without rushing a single tasting or sunset.

This Two Forks, One Weekend itinerary is the route Luxury Beach Getaway recommends most to guests staying across the Hamptons and North Fork. Friday starts in wine country with a farm-to-table dinner near Southold. Saturday’s ferry carries you from Greenport to Sag Harbor. Sunday closes with a Montauk lighthouse morning before the drive west. Every stop below is one we have visited or sent guests to ourselves.

Day 1, Friday Evening: Arrive on the North Fork

The North Fork is the right opening act for an East End weekend. The pace is slower, the wineries are open later than the tasting rooms on the South Fork, and the drive out from the city is about thirty minutes shorter than continuing on to East Hampton. Aim to leave the city by mid-afternoon so you can check in, breathe out, and be at your first tasting before the golden hour.

Bedell Cellars, Cutchogue

Bedell sits on Main Road in Cutchogue, a working vineyard with one of the most polished tasting experiences on the fork. The barn-style room opens onto a wide indoor-outdoor picnic lawn, and weekend afternoons typically include live music. Pair the chardonnay with a charcuterie board and you have an arrival ritual that takes the edge off the drive without rushing the rest of the night.

• Rating: 4.4 stars, 187 reviews
• Address: 36225 Main Rd, Cutchogue, NY 11935
• Hours: Friday and Saturday 11 AM to 7 PM, Sunday to Thursday 11 AM to 6 PM
• Phone: (631) 734-7537
• What to order: Estate chardonnay, taberna red blend, seasonal charcuterie

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Macari Vineyards, Mattituck

If you have time for a second tasting before dinner, drive a few miles west to Macari. The estate stretches across roughly 500 acres along the Peconic Bay side of the fork, and the bayside breeze makes the picnic tables some of the most pleasant outdoor seating in the region. Macari is particularly worth the stop for guests who lean toward whites and rosés, and their sauvignon blanc is consistently among the best on Long Island.

• Rating: 4.5 stars, 466 reviews
• Address: 150 Bergen Ave, Mattituck, NY 11952
• Category: Winery
• What to order: Sauvignon blanc, Lifeforce chardonnay, Rosé

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Dinner at North Fork Table & Inn, Southold

Reserve your Friday dinner well in advance and reserve it here. North Fork Table & Inn has set the bar for destination dining on the fork for nearly two decades, and the seasonal American menu reads like a love letter to the farms and oyster beds within a fifteen-mile radius. The dining room is warm and low lit, the wine list leans local, and after dinner you can walk the gardens before turning in.

• Rating: 4.5 stars, 399 reviews
• Address: 57225 Main Rd, Southold, NY 11971
• Phone: (631) 765-0177
• What to order: Local oysters to start, the seasonal tasting menu, a North Fork chardonnay pairing

A recent guest, Nitzan, called it “the perfect North Fork getaway, the food was exceptional, the hospitality even better.”

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Day 2, Saturday Morning: A Slow North Fork Start, Then the Ferry South

The genius of the Two Forks weekend is the Saturday morning crossing. Instead of driving back west on the Long Island Expressway and looping south through Riverhead, you drive seven minutes onto the North Ferry from Greenport, cross Shelter Island, take a second ferry into North Haven, and step out onto the South Fork in time for lunch in Sag Harbor. The boats save you well over an hour and turn dead transit into one of the prettiest stretches of the weekend.

Love Lane Kitchen, Mattituck

Save Friday’s farm-to-table dinner for an unhurried morning here. Love Lane Kitchen anchors Mattituck’s tiny commercial strip and runs on locally sourced eggs, North Fork bacon, and from-scratch biscuits and pastries. It is the kind of place where the regulars know the staff, and a coffee and a seat by the window is the right way to ease into the day.

• Rating: 4.5 stars, 1,327 reviews
• Address: 240 Love Ln, Mattituck, NY 11952
• Category: American cafe
• What to order: The breakfast sandwich, the granola bowl, a flat white

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Harbes Family Farm, Mattituck

A short detour from Love Lane lands you at Harbes, the most family-friendly farm stand on the fork and a working farm that takes its produce seriously. Pick up jam, sweet corn, and the seasonal cider donuts to take with you, and let the kids burn a half hour in the barnyard before you point the car toward Greenport.

• Rating: 4.3 stars, 704 reviews
• Address: 247 Sound Ave, Mattituck, NY 11952
• What to grab: Sweet corn, apple cider donuts, peach jam, a six-pack of farm eggs

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Lavender By the Bay, East Marion

If you are visiting between mid-June and late July, pull off Main Road in East Marion for the bloom. Twelve acres of lavender stretch toward the bay, and even on a busy summer Saturday it is one of those rare places that quiets every conversation down for a few minutes. Outside peak bloom, the farm shop is still worth a stop for the essential oils, sachets, and lavender honey.

• Rating: 4.4 stars, 666 reviews
• Address: 7540 Main Rd, East Marion, NY 11939
• Best time: Late June through late July for peak bloom
• What to grab: Lavender essential oil, sachets, lavender honey

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Greenport Harbor and the Ferry South

Spend an hour walking Greenport itself. Front Street and Main Street are dense with boutiques, antique shops, and one of the prettiest little carousels in the state. If you have time, stop in at Greenport Harbor Brewing Company for a flight before the ferry. The brewery’s pour list is local in a way that the wineries cannot match, and the front patio looks straight at the harbor.

• Greenport Harbor Brewing Company: 4.6 stars, 157 reviews, 234 Carpenter St, Greenport, NY 11944
• Hours: Typically open daily, check the website for live music nights

View Greenport Harbor

From the ferry dock at the end of Wiggins Street, the North Ferry leaves every fifteen minutes for the seven-minute hop to Shelter Island. Drive straight across the island, with an optional fifteen-minute stop at Mashomack Preserve to stretch your legs in 2,039 acres of woodland, tidal creeks, and salt marsh, then queue for the South Ferry into North Haven.

Mashomack Preserve, Shelter Island

If you can spare ninety minutes between the two ferries, the visitor center loop trail at Mashomack is the right midday reset. Trails are well marked, you will see osprey nests and freshwater ponds, and the entrance fee is a small donation. Bring water and bug spray in summer.

• Rating: 4.8 stars, 307 reviews
• Address: 79 S Ferry Rd, Shelter Island, NY 11964
• Hours: Daily, dawn to dusk
• What to do: Visitor center loop, the green trail (1.5 miles), bird-watching

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Day 2, Saturday Afternoon and Evening: Sag Harbor, the Beach, and a Bridgehampton Dinner

You will step off the South Ferry in North Haven with a fifteen-minute drive into Sag Harbor ahead of you, which is also the most efficient introduction to the Hamptons you can ask for. Park near Main Street, eat by the marina, and let the afternoon unfold.

Sag Harbor Whaling and Historical Museum

The whaling museum sits in a Greek Revival mansion at the head of Main Street, and a thirty-minute tour is a smart investment in context for everything else you will see this weekend. The collection spans scrimshaw, ship’s logs, harpoons, and a recreated nineteenth-century cooper shop, and the docents are sharp.

• Rating: 4.5 stars, 145 reviews
• Address: 200 Main St, Sag Harbor, NY 11963
• Hours: Seasonal, typically open daily late May through Columbus Day
• What to see: The Wickham collection, the captain’s quarters recreation

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Coopers Beach, Southampton

If a real Atlantic beach afternoon is on the agenda, point the car west to Coopers Beach. It is the broadest, sandiest ocean beach on the South Fork, and the parking lot accepts day passes for non-residents. Lifeguards, bathrooms, a snack bar, and a long flat stretch of soft sand make it the easiest place to spend three hours doing absolutely nothing.

• Rating: 4.7 stars, 1,634 reviews
• Address: 268 Meadow Ln, Southampton, NY 11968
• Best time: Arrive before noon on summer weekends for parking
• What to bring: A canopy or umbrella, the snack bar exists but lines build

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Dinner at Almond, Bridgehampton

Almond has been the South Fork’s quiet champion of farmstand cooking for two decades. The dining room is unassuming, the menu names its farms, and the wine list runs deep enough for serious drinkers without becoming intimidating. Reserve early in season, especially for a Saturday night, and ask about the kitchen’s daily fish.

• Rating: 4.4 stars, 312 reviews
• Address: 1 Ocean Rd, Bridgehampton, NY 11932
• Phone: (631) 537-5665
• Hours: Friday and Saturday 5 to 11 PM, Sunday to Wednesday 5 to 9 PM, Thursday 5 to 9:30 PM
• What to order: The mussels, the daily fish prepared “naked,” the hanger steak frites

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Day 3, Sunday Morning: Montauk to the End and Back

Leave the South Fork lodging early. Montauk is at its best before the day-trippers arrive, and the drive from East Hampton to the lighthouse is one of the prettiest forty-five minutes on Long Island, with Napeague stretching wide on either side of the road.

Montauk Point Lighthouse

The Montauk Point Lighthouse has stood at the eastern tip of Long Island since 1796, commissioned by George Washington and still maintained as a working aid to navigation. Climb the 137 iron steps for a 360-degree view that on a clear morning reaches all the way to Block Island, then walk the bluff trail back along the surf line. The museum at the base is worth twenty minutes for the keepers’ quarters reconstruction alone.

• Rating: 4.8 stars, 309 reviews
• Address: 2000 Montauk Hwy, Montauk, NY 11954
• Hours: Seasonal, typically 10:30 AM to 4:30 PM weekends
• What to do: Climb the tower, walk the bluff trail, museum visit

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Main Beach, East Hampton

On the way back west, ten minutes off Montauk Highway, Main Beach is the classic East Hampton beach for a reason. Soft sand, real surf, and a pavilion with showers and a snack bar that punches above its weight. If you only have an hour, go anyway.

• Rating: 4.6 stars, 46 reviews
• Address: 102 Ocean Ave, East Hampton, NY 11937
• Best for: A quick swim and a board walk before lunch

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Parrish Art Museum, Water Mill

The Parrish is the South Fork’s serious art museum, and the Herzog & de Meuron building is itself worth the visit. The collection focuses on the artists who have worked on the East End from the late nineteenth century forward, including Pollock, de Kooning, Krasner, Porter, and Rivers. Plan ninety minutes minimum.

• Rating: 4.5 stars, 621 reviews
• Address: 279 Montauk Hwy, Water Mill, NY 11976
• Hours: Wednesday to Monday 10 AM to 5 PM
• What to see: The permanent East End collection, the current rotating exhibition

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Wolffer Estate Vineyard, Sagaponack

End the weekend where the two forks really do meet in spirit. Wolffer is the most famous winery on the South Fork, the rosé is the signature, and the late-Sunday-afternoon tasting on the lawn is the right way to slow down before the drive home. The barn building and the sloped vineyards are some of the most photographed in the region for good reason.

• Rating: 4.4 stars, 717 reviews
• Address: 139 Sagg Rd, Sagaponack, NY 11962
• What to order: Summer in a Bottle rosé, the estate red, a cheese board

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A Greenport Hold: Claudio’s

If the calendar bends and you want a final North Fork lunch, drive into Greenport for a dockside table at Claudio’s. The space has been a Greenport institution since 1870, the lobster roll is a baseline you should have on the trip somewhere, and the deck looks straight onto the harbor where you took the ferry yesterday.

• Rating: 4.4 stars, 1,667 reviews
• Address: 111 Main St, Greenport, NY 11944
• Phone: (631) 477-0627
• What to order: The lobster roll, raw oysters, a glass of local rosé

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The Right Way to See the East End

The Two Forks weekend works because the East End is, despite the marketing, one place. Same farmstands. Same oyster beds. Same Atlantic. The forks just point in different directions. With one weekend, the right route, and a rental on each side, you get the full picture: the wine country mornings, the harbor afternoons, the ocean swims, and the long quiet drive past the lavender at the end.

When you are ready to plan the stay, browse our East End vacation rentals or reach out directly and our team will match you with the right home on each fork for the weekend you have in mind.

Frequently Asked Questions

Is it really possible to see both the Hamptons and North Fork in one weekend?

Yes, comfortably, as long as you use the Shelter Island ferries instead of driving back through Riverhead. The North Ferry from Greenport plus the South Ferry into North Haven is about twenty-five minutes door-to-door and saves at least ninety minutes of driving.

Which fork should we sleep on first?

Sleep on the North Fork Friday night and the South Fork Saturday night. The North Fork dinner reservations are easier to land on a Friday, and waking up on the South Fork on Sunday puts Montauk inside an easy morning drive.

What is the best season for a Two Forks weekend?

Late May through early October. June and September are the sweet spots: peak winery hours, beach weather, and noticeably fewer crowds than July and August. Lavender By the Bay peaks late June through late July.

How long are the ferry rides between Greenport and the South Fork?

The Greenport to Shelter Island North Ferry runs about seven minutes. The Shelter Island to North Haven South Ferry runs about five to seven minutes. Total transit, including the short drive across Shelter Island, is roughly twenty-five to thirty minutes.

Do we need a beach permit for Coopers Beach or Main Beach?

Both beaches require a daily parking fee for non-residents. Coopers Beach in Southampton sells day passes at the gate. Main Beach in East Hampton requires either a day pass or a non-resident parking pass that you can buy at East Hampton Town Hall during the week.

What if we want to add a fourth day?

Add it on the North Fork. A second North Fork day rewards a slow morning at Orient Beach State Park, a long lunch at one of our recommended waterfront spots, and a final tasting at Sparkling Pointe or Croteaux Vineyards. Our Longer Stays collection is built for exactly this kind of trip extension.

There is a particular kind of quiet that settles over the North Fork when it rains. The vineyards go still, the bay turns the color of slate, and the Main Road empties out into something close to the version of itself that locals know best. If you have been wondering what to do on the North Fork when it rains, the answer is rarely “wait it out.” The answer is to slow down, change pace, and let the weather hand you back the kind of afternoon a busy summer almost never allows.

We have spent close to twenty years welcoming guests to the East End, and the rainy day itinerary is the one we end up writing most often. It is a soft circuit of sparkling wine in candlelit tasting rooms, used books and curated antiques, hot coffee with the windows fogging up, and one long, unhurried meal. Below is the version we share with friends and the version we send to guests staying in one of our North Fork vacation rentals when the forecast turns gray.

Tasting Rooms Built for a Slow, Indoor Afternoon

The wineries that work hardest on a sunny Saturday, with their tented patios and lawn chairs, are not always the ones that shine in the rain. The places below were built around their interiors. Big windows, working fireplaces, polished bars, and the kind of seated tastings that reward staying a while.

Sparkling Pointe (Southold)

If you are only going to make one stop, make it Sparkling Pointe. The tasting room is all soft light, high ceilings, and large windows that turn even a downpour into something worth watching. The house specializes exclusively in traditional method sparkling wines, which is to say the kind of bubbles that ask you to sit down and pay attention.

• Rating: 4.5 stars (342 reviews)
• Address: 39750 County Rd 48, Southold, NY 11971
• Hours: Daily, 11 AM to 5 PM (until 7 PM on Mondays)
• Phone: (631) 765-0200
• What to order: A seated flight of the Brut, Blanc de Blancs, and Topaz rosé, with a cheese pairing
• Google Maps: View on Google Maps

Raphael (Peconic)

Raphael is the closest thing the North Fork has to an Old World wine hall. The building was inspired by a Tuscan monastery, all stone, beamed ceilings, and an atmospheric tasting room that simply feels right when the sky is gray. The wines are Bordeaux-leaning, with structured Merlots and Cabernet Francs that show especially well in the cooler air.

• Rating: 4.3 stars (232 reviews)
• Address: 39390 Main Rd, Peconic, NY 11958
• What to order: A guided flight of the estate reds, especially the First Label Merlot
• Google Maps: View on Google Maps

Bedell Cellars (Cutchogue)

Bedell is the most gallery-like winery on the Fork. A renovated barn with white walls, contemporary art rotating on loan, and a polished bar that flows into seated areas. The estate-grown Merlots are the calling card, but the aromatic whites (Viognier, Sauvignon Blanc) are quietly excellent on a wet afternoon.

• Rating: 4.4 stars (186 reviews)
• Address: 36225 Main Rd, Cutchogue, NY 11935
• What to order: The Musée Reserve flight, with a charcuterie board
• Google Maps: View on Google Maps

Macari Vineyards (Mattituck)

Macari sits on roughly 500 acres of biodynamically farmed land, but the part that matters today is the lounge-style indoor tasting room. Family-run since 1995, with age-worthy reds (especially Cabernet Franc) and a hospitality team that handles weather-day crowds with grace.

• Rating: 4.5 stars (460 reviews)
• Address: 150 Bergen Ave, Mattituck, NY 11952
• What to order: A mixed flight pairing the Sauvignon Blanc with the Bergen Road red blend
• Google Maps: View on Google Maps

Ask about a mixed red and white flight if you cannot decide. The staff are skilled at building one on the spot.

A Detour for Spirits: Two Distilleries Worth the Drive

When you have already had a glass or two of wine, a working distillery is the perfect palate change. Both of these are very much indoor experiences, with copper stills you can see from the bar and a noticeably different rhythm from the wineries.

Long Island Spirits (Baiting Hollow)

The state’s first farm distillery, Long Island Spirits is home to LiV Vodka, Rough Rider whiskies, and a tasting room that doubles as a small live music venue on certain weekends. The indoor bar has the warmth of a country roadhouse, and the cocktails are smartly built around the house spirits.

• Rating: 4.4 stars (57 reviews)
• Address: 2182 Sound Ave, Baiting Hollow, NY 11933
• What to order: A flight of the Pine Barrens American Single Malt with a Rough Rider Bull Moose Three Barrel cocktail
• Google Maps: View on Google Maps

Matchbook Distilling Co. (Greenport)

Matchbook is the experimental wing of the North Fork spirits scene. They produce small-batch, sometimes one-off bottlings using local botanicals and unusual co-fermentations, and the distillery floor is part of the visitor experience. Curious drinkers will spend an hour here easily.

• Rating: 4.5 stars (22 reviews)
• Address: 64755 Main Rd, Greenport, NY 11944
• What to order: Whatever the team is most excited about that week, plus their signature Moon Blight nocino
• Google Maps: View on Google Maps

Bookshops and Browsing for the Long, Slow Hour

A rainy afternoon is the bookshop’s natural element. The North Fork has held onto its independent stores in a way most coastal towns have not, and each one rewards the kind of slow browsing the weather is practically forcing on you.

Burton’s Bookstore (Greenport)

Burton’s has been the heart of the Greenport reading life since 1979. It is compact, friendly, and the staff have read what is on the shelves. New fiction, nonfiction, deeply stocked children’s and local-interest sections, and a sticker selection that has become its own small attraction.

• Rating: 4.9 stars (72 reviews)
• Address: 43 Front St, Greenport, NY 11944
• What to look for: New literary fiction, North Fork and nautical local-interest titles, and a staff recommendation card
• Google Maps: View on Google Maps

Forked Road Press (Southold)

A newer addition to the Main Road and already one of our favorite stops. Forked Road is part bookshop, part record store, part curated knickknack hunt. The collection skews toward rare and unusual finds, and the proprietor, Nick, has built a space that genuinely rewards the time you give it.

• Rating: 5.0 stars (11 reviews)
• Address: 53975 Main Rd, Southold, NY 11971
• Hours: Thursday through Monday, 11 AM to 5 PM (closed Tuesday and Wednesday)
• What to look for: Rare records, vintage paperbacks, and small-batch printed ephemera
• Google Maps: View on Google Maps

Antique Shops and Galleries: The Treasure Hunt Indoors

The North Fork’s antique scene is one of its quietly best-kept aspects. These are not slick design boutiques. They are layered, sometimes crowded, sometimes immaculate rooms full of objects with histories. The rain only makes the lights inside look better.

The Times Vintage (Greenport)

The Times is the Greenport vintage shop everyone names first. Racks of carefully sourced vintage clothing, a strong record selection, and a curatorial eye that turns the whole store into something between a boutique and an installation. Plan to dig.

• Rating: 4.8 stars (105 reviews)
• Address: 429 Main St, Greenport, NY 11944
• What to look for: Statement vintage pieces, bohemian decor, and one-of-a-kind records
• Google Maps: View on Google Maps

Beall & Bell (Greenport)

Across the street from The Times, Beall & Bell is the more polished half of the Greenport antiquing duo. Virginia and Ken have run the shop for years, and their reputation for taste is well earned. Furniture, lighting, ceramics, and a constantly changing roster of high-end vintage objects.

• Rating: 4.4 stars (14 reviews)
• Address: 430 Main St, Greenport, NY 11944
• What to look for: Mid-century furniture, lamps, and small ceramics
• Google Maps: View on Google Maps

Antiques & Old Lace (Cutchogue)

If you have the appetite for a long, careful antique session, drive west to Cutchogue. Antiques & Old Lace has been on Main Road for years and remains one of the most loved antique stops on Long Island. Multiple rooms, deep inventory, and the unhurried rhythm of a true collector’s shop.

• Rating: 4.4 stars (17 reviews)
• Address: 31935 Main Rd, Cutchogue, NY 11935
• Hours: Wednesday and Thursday 11 AM to 4 PM, Friday through Sunday 12 to 4 PM
• What to look for: Antique furniture, vintage glass, old books, and decorative pieces
• Google Maps: View on Google Maps

Alex Ferrone Gallery (Cutchogue)

If the antique density gets to be too much, the antidote is a few blocks east. Alex Ferrone Gallery is a contemporary photography and mixed-media space, with rotating exhibitions and the kind of clean, contemplative interior that gives your eyes a place to rest.

• Rating: 5.0 stars (11 reviews)
• Address: 25425 Main Rd, Cutchogue, NY 11935
• Hours: Friday and Sunday 12 to 5 PM, Saturday 12 to 7 PM
• What to see: Whatever solo or group photography exhibition is currently up
• Google Maps: View on Google Maps

Cafes Designed for Lingering

The mid-afternoon reset. Wherever you started the day, plan to put an hour into one of these for hot coffee, something baked, and the quiet pleasure of watching the rain.

Aldo’s Coffee Company (Greenport)

Aldo’s is the Greenport coffee institution. Strong espresso, a small but well-built food menu, and a seating area that has been refined over years into something genuinely comfortable. Coffee-bag cushions, local art on the walls, and the kind of staff who remember your order on the second visit.

• Rating: 4.5 stars (525 reviews)
• Address: 103-105 Front St, Greenport, NY 11944
• Hours: Monday through Thursday 7 AM to 5 PM, Friday and Saturday until 8 PM, Sunday until 6 PM
• What to order: A strong Americano and one of the morning pastries
• Google Maps: View on Google Maps

North Fork Roasting Co. (Southold)

The roastery and cafe locals send you to when you ask, plainly, where to get the best coffee on the Fork. The space is warm, well-lit, and easy to settle into for an hour with a book. Order the iced vanilla latte that everyone talks about, even in the rain.

• Rating: 4.7 stars (309 reviews)
• Address: 55795 Main Rd, Southold, NY 11971
• What to order: An iced vanilla latte (it is not just a summer drink here) and an avocado toast
• Google Maps: View on Google Maps

A Long Meal: The Best Excuse to Stop Watching the Sky

If the rain is going to settle in for the evening, you have a perfect reason to book the kind of dinner you usually save for special occasions. These two are the long-meal recommendations we make most often.

Love Lane Kitchen (Mattituck)

The morning and lunch anchor of Mattituck’s Love Lane. Stained wood, blackboard specials, and a kitchen that handles a busy Sunday brunch with the same care as a quiet Tuesday breakfast. Locals consider it essential, which is reason enough.

• Rating: 4.5 stars (1,323 reviews)
• Address: 240 Love Ln, Mattituck, NY 11952
• What to order: The Love Lane breakfast burrito, or for lunch the lobster roll
• Google Maps: View on Google Maps

North Fork Table & Inn (Southold)

If you are going to have one big dinner on the Fork, have it here. The dining room is small, warm, and built for the kind of long, three-hour meal that ends with you ordering one more glass of wine and not minding the drive home. The menu changes constantly and leans into what is in season locally.

• Rating: 4.5 stars (397 reviews)
• Address: 57225 Main Rd, Southold, NY 11971
• What to order: The tasting menu, if you can, with the local wine pairing
• Google Maps: View on Google Maps

How to Sequence a Rainy Day on the North Fork

The trick is to pick one town as your base and stay close. Driving long stretches of Sound Avenue or Route 25 in a downpour is the opposite of restful. Three loops that work:

The Greenport Loop. Coffee at Aldo’s, book browsing at Burton’s, a slow hour through The Times Vintage and Beall & Bell, sparkling wine at Sparkling Pointe a short drive west, and dinner back in the village. Almost entirely walkable in the village portion.

The Cutchogue and Peconic Loop. Begin at Bedell Cellars for the late-morning flight, move next door to Antiques & Old Lace, pause at Alex Ferrone Gallery, and finish at Raphael for a final tasting before dinner.

The Mattituck and Southold Loop. A long breakfast at Love Lane Kitchen, coffee at North Fork Roasting Co., book and record browsing at Forked Road Press, a tasting at Macari, and a celebratory dinner at North Fork Table & Inn.

A Final Word

The locals do not curse the rain on the North Fork. They plan for it. The vineyards built their tasting rooms to handle it, the bookshops have been hoping for it all week, and the kitchens are at their best when there is no pressure to turn the table. If the forecast is gray for your stay, take it as permission to slow down. The Fork is built for it.

When you are ready to plan a trip, take a look at our North Fork vacation rentals. We have spent nearly twenty years curating homes that hold up to the kind of weather that asks you to stay inside, and we will happily help you pick the right one.

Frequently Asked Questions

What is the best thing to do on the North Fork when it rains?

Build the day around indoor tasting rooms (Sparkling Pointe, Raphael, Bedell), a stop at Burton’s Bookstore or Forked Road Press, and a long meal at Love Lane Kitchen or North Fork Table & Inn. Pick one village (Greenport, Southold, or Mattituck) as the base to keep driving to a minimum.

Are North Fork wineries open in the rain?

Yes. Most of the major tasting rooms operate year-round and were designed with substantial indoor space. Sparkling Pointe, Raphael, Bedell, Macari, and Pindar all have polished indoor tasting areas. Reservations become more important on rainy weekends because more visitors choose to be inside.

What are the best North Fork bookshops?

Burton’s Bookstore in Greenport (since 1979) is the classic stop for new books and local titles. Forked Road Press in Southold is the newer, more eclectic option, combining books, records, and curated knickknacks under one roof.

Where can I find antique shops on the North Fork?

The two most established clusters are along Main Street in Greenport (The Times Vintage, Beall & Bell, and the Weathered Barn) and along Main Road in Cutchogue (Antiques & Old Lace). Plan at least an hour for each cluster, more if you are a serious antiquer.

Is the North Fork worth visiting in the off-season?

Absolutely. Shoulder season and even winter visits offer empty tasting rooms, easier dinner reservations, and a quieter, more local version of the Fork. Many of the indoor activities in this guide were built for exactly that kind of trip.

How far is the North Fork from the Hamptons in bad weather?

The two forks of the East End are roughly thirty to forty-five minutes apart by car using the South Ferry or the longer drive around through Riverhead. In heavy rain, the drive through Riverhead is the safer choice.

There is a particular kind of New York village that asks very little of you, and gives back a lot. Greenport, the working harbor at the tip of the North Fork, is that kind of place. One square mile of historic streets, a marina humming with fishing boats and ferries, a carousel that has been spinning for more than a century, and oysters pulled out of the bay that morning. It earns every hour you give it, whether you have a long afternoon or a slow three-day weekend.

This guide is built for guests staying in our boutique vacation rentals across the North Fork and the Hamptons. We have spent nearly twenty years sending visitors east to this village, and the rhythm is always the same: arrive, slow down, eat well, walk the docks at sunset. What follows is the version of Greenport our team recommends to friends, organized by the experiences that consistently earn the loudest thanks in our guest reviews.

Why Greenport Rewards a Slow Visit

Greenport is technically an incorporated village inside the Town of Southold, but it functions like a self-contained world. The historic district holds more than 200 protected buildings, some dating to the mid-1700s, and the streetscape has been preserved with unusual care. Main Street and Front Street form the spine, the harbor sits at the foot of both, and almost everything worth doing is reachable on foot from any anchor point.

That density is what makes the village work for short, unhurried visits. You do not need to plan a complicated itinerary. You can park once, walk a half-mile loop past the carousel, the marina, the oyster bar, the brewery, and the seaport museum, and still circle back to your starting point for a drink before dinner. Guests staying at our North Fork vacation rentals often tell us this is the unexpected joy of Greenport, that for a place packed with this much history and food culture, it never feels like work.

Harbor, History, and the Heart of the Village

Start where Greenport itself begins, at the water. This first cluster of stops sits within a five-minute walk of the marina and frames every other thing you will do in the village.

Mitchell Park and Marina

If Greenport has a living room, this is it. Mitchell Park is the harborfront green that anchors the village, with a boardwalk, open sightlines to Shelter Island, and the small marina where visiting yachts, fishing boats, and the Shelter Island North Ferry all share space. Locals call this the easiest way to take the temperature of the village in any given hour: at noon it is families on benches with ice cream, at dusk it turns into a slow-moving sunset crowd.

• Rating: 4.6 stars across 141 Google reviews
• Address: 115 Front St, Greenport, NY 11944
• Hours: Open daily, dawn to dusk
• Best for: Sunset walks, watching the ferry traffic, picnic lunches
• View on Google Maps

Antique Carousel at Mitchell Park

Tucked inside a glass pavilion at the edge of the park, the Greenport Antique Carousel is more than a century old and still spins on weekends. Rides are inexpensive, the ride itself is short, and the pleasure is almost entirely in the ritual: handing a child a token, watching them grab for the brass ring, and stepping out into a harbor view at the end. It is the kind of small thing that ends up at the top of guests’ photo rolls.

• Rating: 4.6 stars across 263 Google reviews
• Address: 115 Front St, Greenport, NY 11944
• Hours: Saturday and Sunday, 11 AM to 5 PM (seasonal expansion in summer)
• Phone: (631) 477-0248
• Best for: Families, photographers, anyone with a soft spot for old things done well
• View on Google Maps

East End Seaport Museum and Marine Foundation

A short walk from the carousel sits the East End Seaport Museum, housed in a former Long Island Rail Road station near the ferry docks. Inside you will find one of the better small-museum collections on the East End, with exhibits on local lighthouses, the oyster industry, and the wartime shipyards that once defined the village. Admission is free, the docents are the kind of locals who actually remember the shipyard era, and the whole experience takes about forty minutes.

• Rating: 4.6 stars across 89 Google reviews
• Address: 3rd St, Greenport, NY 11944
• Phone: (631) 477-2100
• Website: eastendseaport.org
• Hours: Wednesday through Monday, generally 10:30 AM to 5 or 6 PM (closed Tuesdays)
• Best for: Rainy mornings, maritime history readers, families with curious kids
• View on Google Maps

67 Steps Beach

Sixty-seven steps down a wooden staircase, on the Long Island Sound side of the village, opens onto a rocky beach that locals quietly treat as their sunset spot. There are no facilities, parking requires a permit, and the shoreline is more boulders than soft sand, which is precisely why it stays uncrowded. Bring water shoes, a sweater for after dark, and a sense of patience. The pay-off is one of the most uninterrupted Sound views on the North Fork.

• Rating: 4.6 stars across 282 Google reviews
• Address: 66 Sound Rd, Greenport, NY 11944
• Hours: 6 AM to 10 PM daily
• Best for: Sunset, photography, quiet evenings
• View on Google Maps

Where to Eat and Drink in Greenport

Food is the second reason Greenport earns its hours. The village has more restaurant talent per block than most towns three times its size, and the oysters lifted out of the surrounding bays are still the headline ingredient. Below are the addresses we recommend most often.

Claudio’s Waterfront

Claudio’s has been on the same Main Street dock for generations, and at this point it functions as the village’s central reservation. The dining room is open-air, the wraparound deck looks straight onto Greenport Harbor, and the menu plays to what the kitchen does well: clam chowder, fried seafood platters, classic raw bar, lobster done several ways. It is the place to come for a long midday lunch with a view, ideally before everyone else thinks to do the same.

• Rating: 4.5 stars across 2,575 Google reviews
• Address: 111 Main St, Greenport, NY 11944
• Phone: (631) 477-0627
• Website: claudios.com
• Hours: Daily, 11 AM to 9:45 PM Friday and Saturday (shorter midweek hours)
• What to order: Clam chowder, fish tacos, lobster salad, the fried seafood plate
• View on Google Maps

Little Creek Oyster Farm and Market

If you only have time for one stop in Greenport, this should be it. Little Creek is a small, wood-walled oyster shack on the harbor where you can sit at the counter and watch the team shuck through the dozen-plus local varieties they keep in rotation. There is a tight wine and beer list, a couple of warm dishes for non-shellfish eaters, and an upstairs patio that catches the breeze in summer. The vibe is exactly the unpolished, ingredient-first North Fork experience guests rave about.

• Rating: 4.8 stars across 496 Google reviews (one of the highest-rated spots in the village)
• Address: 211 Carpenter St, Greenport, NY 11944
• Phone: (631) 477-6992
• Website: littlecreekoysters.com
• Hours: Friday and Saturday, 12 to 9 PM; Sunday 12 to 8 PM; Wednesday and Thursday 5 to 9 PM; closed Mondays and Tuesdays
• What to order: A varied half-dozen of local oysters, plus a glass of North Fork rosé
• View on Google Maps

Noah’s

Front Street’s small-plates flagship, Noah’s has been a benchmark for North Fork dining since it opened. The menu reads like a love letter to the East End pantry: oysters and clams from the bay, vegetables from Long Island farms, a tight selection of regional wines. Order broadly across the small plates, share, and pace yourself. Reservations are wise on weekend nights from late spring through fall.

• Rating: 4.3 stars across 583 Google reviews
• Address: 136 Front St, Greenport, NY 11944
• Phone: (631) 477-6720
• Website: chefnoahs.com
• Hours: Open most evenings, 5 to 9 PM (open earlier on weekends); closed Wednesday
• What to order: The raw bar, the filet mignon sliders, anything seasonal
• View on Google Maps

Bruce and Son

Greenport’s brunch and serious-coffee corner. The kitchen at Bruce and Son leans into seasonal, farm-driven plates: there is a sugar-bacon egg sandwich with pickled onions that guests bring up unprompted weeks after their stay, plus a small but interesting breakfast menu and a coffee program that respects its ingredients. The room is small, the line moves, and the payoff is the kind of weekend breakfast you remember.

• Rating: 4.4 stars across 345 Google reviews
• Address: 208 Main St, Greenport, NY 11944
• Website: bruceandsongreenport.com
• Hours: Open most days 9 AM to 2:30 PM; closed Tuesday and Wednesday
• What to order: The egg sandwich with sugar bacon, the carrot lox sandwich, a bourbon latte
• View on Google Maps

Wine, Beer, and a Boutique Hotel Worth Knowing

A short walk or a five-minute drive from the harbor opens up the village’s drinking culture: the only true waterfront winery on the North Fork, a small-batch brewery in a converted firehouse, and the boutique hotel that has quietly become the social hub of Stirling Square.

Kontokosta Winery

Sixty-two acres on a bluff above the Long Island Sound, with the only quarter-mile of true waterfront on the North Fork wine trail. Kontokosta is what you pull out for guests who want a vineyard experience that does not feel manicured: open-air tasting room, ocean breeze, live music on weekends, and a small estate-grown lineup that includes their Anonometer blends and a respected white Cabernet Franc. Plan for late afternoon, sit outside, and time your visit so you are still there when the wind shifts off the water.

• Rating: 3.8 stars across 534 Google reviews
• Address: 825 North Rd, Greenport, NY 11944
• Phone: (631) 477-6977
• Website: kontokostawinery.com
• Hours: Daily, 11 AM to 5 PM
• What to order: A flight of the estate-grown whites and the Anonometer red blend
• View on Google Maps

If wineries are the through-line of your trip, our Wine Country vacation rentals put you within fifteen minutes of every major North Fork tasting room, so the drive home is short and the cellars are open.

Greenport Harbor Brewing Company (Carpenter Street Taproom)

The original Greenport Harbor location on Carpenter Street is the kind of brewery that earns its loyalty. The tasting room is upstairs and intimate, the downstairs has a casual lived-in feel with a small stage for weekend bands, and the beer list reflects what the brewers actually want to be making. The Tumbleweed Tuesdays habit (the rare weekday opening), the rotating dark beers, and the small but well-curated merch table all add up to a stop that lands in guests’ photo rolls.

• Rating: 4.6 stars across 157 Google reviews
• Address: 234 Carpenter St, Greenport, NY 11944
• Phone: (631) 477-1100
• Website: greenportharborbrewing.com
• Hours: Friday and Saturday, 12 to 8 PM; Sunday 12 to 7 PM; check ahead for Tumbleweed Tuesdays
• What to order: Whichever local-only pour is on the chalkboard, plus the coffee-chocolate dark beer when in season
• View on Google Maps

American Beech (Stirling Square)

Two blocks off the harbor, American Beech is the boutique hotel and restaurant that anchors Stirling Square. Even if you are not staying there, the courtyard, the cocktail program, and the restaurant are worth knowing about: a stylish open-air dinner setting on a warm night, with attentive service and a modern American menu that pulls heavily from the local pantry. It is also the easiest place in the village to land a confident pre-dinner drink.

• Rating: 4.5 stars across 625 Google reviews
• Address: 302 Main St, Greenport, NY 11944
• Phone: (631) 477-5939
• Website: americanbeech.com
• What to order: Duck tagliatelle, blackened mahi, an after-dinner brownie sundae with mascarpone
• View on Google Maps

A Suggested Two-Day Greenport Itinerary

The point of Greenport is that you do not need a tight schedule, but if you would like a frame to push against, here is the rhythm our guests tend to land on.

Saturday

• 9:00 AM: Coffee and the sugar-bacon egg sandwich at Bruce and Son.
• 10:30 AM: Walk Front Street to the East End Seaport Museum. Forty unhurried minutes.
• 11:30 AM: Loop through Mitchell Park, ride the Antique Carousel if you have a kid in tow, watch the Shelter Island North Ferry come and go.
• 12:30 PM: A dozen oysters and a glass of rosé at Little Creek.
• 2:30 PM: Drive to Kontokosta Winery on the Sound. Sit outside.
• 5:30 PM: Back into the village. A pre-dinner drink at the American Beech courtyard.
• 7:30 PM: Dinner at Noah’s. Order broadly.

Sunday

• 8:30 AM: Quiet walk along the harbor.
• 10:00 AM: Brunch at Claudio’s, claim a table on the dock.
• 12:30 PM: Browse the Main Street boutiques and galleries between Stirling and Third Street.
• 3:00 PM: Take the North Ferry across to Shelter Island, even if you only stay for the round trip.
• 5:00 PM: Beer flight and weekend music at Greenport Harbor Brewing.
• 7:30 PM: Sunset at 67 Steps Beach. Bring water shoes and a sweater.

If you have a Friday or a Monday in the mix, swap in a drive to Orient Point at the very tip of the North Fork, an antique-hunting loop through Southold, or a slow morning at the Greenport Farmers’ Market in Mitchell Park (Saturdays in season).

Practical Tips Before You Go

A few small things our concierge team mentions on almost every call.

• Drive in from the west. The Long Island Expressway thins out east of Riverhead. Allow two and a half to three hours from Manhattan in summer traffic, less on a weekday.
• Or take the train. The Long Island Rail Road’s Ronkonkoma branch terminates at Greenport. The station is a one-minute walk from the seaport museum and a five-minute walk from Mitchell Park.
• Park once and walk. The historic district is dense and parking turns over slowly. Find a spot near Mitchell Park or Stirling Square and leave the car for the afternoon.
• Reservations matter from May through October. Noah’s, Claudio’s, and American Beech all fill quickly on weekend nights. Book ahead.
• Pack layers, even in July. Sound-side beaches like 67 Steps cool off fast after sunset.

Plan Your North Fork Stay

Greenport rewards guests who give it room to unfold. The historic district, the harbor, the oysters, the carousel, and the Sound-side sunsets all live within a square mile, but each one earns its own slow visit. Pair the village with a few days in a private North Fork rental and the weekend turns into something guests remember for years.

When you are ready to plan, our team can match you with the right home for your dates and walk you through the corners of the village that do not make it into any guidebook. Browse our North Fork vacation rentals, or reach out to our team and we will help you build a Greenport weekend around the things you actually want to do.

Frequently Asked Questions

Is Greenport worth visiting for a day trip from NYC?

Yes, comfortably. The Long Island Rail Road terminates a five-minute walk from the harbor, so a Saturday round trip is realistic without a car. The village is dense enough that a single day covers a museum stop, lunch on the dock, a carousel ride, and a sunset walk before the train back. A two-day visit is the sweet spot, but a day trip is genuinely satisfying.

What is Greenport, NY known for?

Greenport is known for its working harbor, its preserved 19th-century historic district, the Antique Carousel at Mitchell Park, the Long Island oyster industry, and a dense cluster of waterfront restaurants and small-batch craft producers. It is one of the only North Fork towns where the maritime heritage is still actively in use, not just commemorated.

When is the best time of year to visit Greenport?

Late May through mid-October is the most active window, with all restaurants, the carousel, the farmers’ market, and outdoor wineries in full swing. September and early October are the quietest of the busy months, with harvest at the wineries and noticeably thinner crowds. Winter visits work for guests looking for off-season calm, a tree-lighting weekend in December, and serious off-season pricing on rentals.

How do you get from Greenport to Shelter Island?

The Greenport-Shelter Island North Ferry departs from the village waterfront just south of Mitchell Park. The crossing is short, roughly five to ten minutes, and runs year-round. Walk-on passengers, bicycles, and cars are all accommodated, and the ride itself doubles as the easiest scenic boat tour in town.

Can you visit Greenport without a car?

Yes. The Long Island Rail Road’s Greenport station puts you within a five-minute walk of every restaurant, museum, and waterfront stop in this guide. The North Ferry takes walk-on passengers, and the village is genuinely walkable. The only car-only stops in this guide are Kontokosta Winery and 67 Steps Beach, both of which are reachable by short rideshare from the harbor.

How many oysters should I order at Little Creek?

The house move is a half-dozen of mixed varieties per person, with a glass of North Fork rosé or sparkling. If you are settling in for a full meal, double it and add the warm small plates. The team will walk you through what came in that morning and what is at peak flavor.

If you are planning a summer stay on the East End, the Hamptons art scene in summer is not a sidebar to the beach days. It is one of the main events. From the architectural grandeur of the Parrish Art Museum in Water Mill to the intimate, plein-air realism of Sag Harbor’s Grenning Gallery, the entire region functions as a single, dispersed open-air museum across roughly fifty miles of coastline.

This guide, curated by our team after nearly twenty years of welcoming guests to the Hamptons and North Fork, walks you through the museums, gardens, foundations, and galleries that define a summer art itinerary in 2026. We have included current 2026 exhibitions, real visitor reviews, addresses, hours, and a few quiet local recommendations on how to pace your days so you can actually enjoy them.

The Marquee Summer Art Event: Hamptons Fine Art Fair 2026

Anchor your trip around one event and it should be this one. The Hamptons Fine Art Fair returns to the Southampton Fairgrounds at 605 County Road 39 from July 9 to 12, 2026, for its 19th edition. The 2026 fair features roughly 140 galleries from about twenty countries, with a deep program spanning post-war, contemporary, and emerging artists. Spotlight presentations include Julian Lennon (Fremin Gallery), Henry Orlik (Winsor Birch), Mel Ramos (Louis K Meisel Gallery), Bert Stern (The Gallery), and a Keith Haring program from Link Fine Art.

New for 2026 is SculptureHamptons, a satellite outdoor program staged at LongHouse Reserve in East Hampton. Expect glass, ceramics, metalworks, and large-scale wood from more than twenty international galleries set across the 16-acre sculpture garden. The Opening Night Vernissage benefits Guild Hall and is consistently one of the most photographed evenings of the East End summer.

If your stay overlaps with the second weekend of July, book timed tickets early and plan a quiet morning beforehand. The fair is a marathon, and pacing matters.

Museums and Foundations: The Anchor Institutions

Parrish Art Museum

Designed by Swiss firm Herzog and de Meuron and conceived as an oversized, abstracted barn, the Parrish Art Museum is the institutional heart of the Hamptons art world. Its long zinc roof and skylit galleries house one of the strongest collections of East End and 20th-century American art anywhere in the country.

Summer 2026 brings several major exhibitions: The Barn: Desert Weave (opening June 5), Tony Bechara’s An Artist of Many Worlds (member opening June 28), a focused presentation of Sean Scully abstractions reflecting on the summer he spent in Montauk in 1982, and Shirin Neshat’s portrait photography, her first New York-area show in twenty years. Headline events include the Midsummer Gala on July 18, the Savor the Summer community day on June 14 with free admission, the Summer Jazz series, and Art Splash on August 15.

• Rating: 4.5 stars (619 reviews)
• Address: 279 Montauk Highway, Water Mill, NY 11976
• Hours: Thursday to Monday, 11 AM to 5 PM; closed Tuesday and Wednesday
• Phone: (631) 283-2118
• Don’t miss: Coffee and a snack at the Parrish cafe, then a long sit on the outdoor wall facing the meadow
• Insider tip: Visitors with a SNAP/EBT card are admitted free

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Guild Hall

Open year-round on East Hampton’s Main Street, Guild Hall is the cultural town square of the East End: gallery, theater, lecture hall, and community center rolled into a single elegant building. The 2026 summer program includes Functional Relationships: Artist-Made Furniture, Almond Zigmund’s Wading Room, and the highly anticipated Student Art Festival: Rauschenberg100.

Beyond the visual art, Guild Hall hosts artist talks, intimate music programs, and silent disco nights that have become a summer tradition. As one recent guest described an evening here: “An incredible evening of light and beautiful music. The venue was intimate, cozy and the candles made it magical.”

• Rating: 4.8 stars (158 reviews)
• Address: 158 Main Street, East Hampton, NY 11937
• Phone: (631) 324-0806
• Why we send guests: It is the rare Hamptons institution that is fully open in shoulder seasons too, so a return visit in September stays just as rich

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LongHouse Reserve

Founded by the late textile designer Jack Lenor Larsen, LongHouse Reserve is sixteen acres of sculpture garden, allée, dune planting, and reflecting pool, woven around a residence inspired by a 7th-century Japanese shrine. Yoko Ono’s Play It By Trust chessboard, Willem de Kooning’s Reclining Figure, Buckminster Fuller geometry, and dozens of seasonal installations live among the trees.

The summer 2026 highlight is SculptureHamptons, staged in tandem with the Hamptons Fine Art Fair from July 9 to 12, bringing pieces from more than twenty international galleries into the gardens. Even outside that window, LongHouse is one of the most peaceful art experiences on the East End.

• Rating: 4.9 stars (357 reviews)
• Address: 133 Hands Creek Road, East Hampton, NY 11937
• Phone: (631) 329-3568
• What to wear: Walking shoes, a sunhat, and something you can stretch out on the grass in

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The Watermill Center

The late director Robert Wilson’s Watermill Center is part artist residency, part private collection, part performance laboratory. Set on 11 wooded acres in Water Mill, the center holds a sprawling collection of African, Asian, and contemporary works installed across galleries, gardens, and hidden alcoves. The current exhibition, Upside Down Zebra, curated by Brian Belott and Noah Khoshbin, explores the artistic value of children’s imagination and its influence on contemporary art, drawing on the Rhoda Kellogg International Child Art Collection.

Tours are by appointment, which keeps groups small and the experience deeply personal.

• Rating: (See Google reviews)
• Address: 39 Water Mill Towd Road, Water Mill, NY 11976
• Visit by appointment: Book guided tours in advance
• Don’t miss: The annual summer benefit, a long-running marquee event that doubles as a living performance piece

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The Church

Housed in a meticulously restored 1835 Methodist church in Sag Harbor and reimagined by painter Eric Fischl and writer April Gornik, The Church is one of the most thoughtful additions to the East End art scene in the past decade. The current Fischl-curated exhibition gathers fifty animal sculptures by artists including Louise Bourgeois, Maurizio Cattelan, William Kentridge, Bruce Nauman, Kiki Smith, Sherrie Levine, and Joan Brown.

• Rating: 4.7 stars (50 reviews)
• Address: 48 Madison Street, Sag Harbor, NY 11963
• Phone: (631) 919-5342
• Best paired with: A walk along Long Wharf and lunch in the village afterward

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Pollock-Krasner House and Study Center

The barn studio in Springs where Jackson Pollock made Autumn Rhythm and Convergence, and where Lee Krasner painted after his death in 1956, is one of the most affecting historical sites in American art. The floor of the studio is still pocked with drips and splatter from both painters. Tours run on a reservation basis through summer.

• Rating: 4.5 stars (130 reviews)
• Address: 830 Springs Fireplace Road, East Hampton, NY 11937
• Phone: (631) 324-4929
• Tip: Reserve well in advance; tour slots are limited and frequently sell out in July and August

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Dia Bridgehampton (Dan Flavin Art Institute)

A small but essential stop: the Dia Art Foundation’s Dan Flavin Art Institute occupies a restored former firehouse in Bridgehampton and showcases nine permanent fluorescent light installations by the artist on its upper floor. It is one of the only places in the world where you can see Flavin’s work installed precisely as he conceived it.

• Rating: 4.7 stars (60 reviews)
• Address: 23 Corwith Avenue, Bridgehampton, NY 11932
• Phone: (212) 989-5566
• Cost: Free admission
• Local detail: Pair the visit with an ice cream stop across the street, a long-standing summer ritual

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Southampton Arts Center

The handsome Southampton Arts Center occupies the former Parrish building on Jobs Lane and operates as a year-round gallery, performance space, and outdoor sculpture park. The 2026 summer program continues to balance ambitious contemporary group shows with film screenings, family days, and live music in the courtyard.

• Rating: 4.7 stars (117 reviews)
• Address: 25 Jobs Lane, Southampton, NY 11968
• Phone: (631) 283-0967
• Why visit: It is one of the most centrally located cultural venues in the village, easy to combine with shopping or a meal nearby

A recent reviewer praised the curatorial vision: the current show “really nails it, an honest response to what’s going on culturally right now, with artists from all kinds of backgrounds.”

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Peter Marino Art Foundation

Architect Peter Marino’s Art Foundation is around the corner from the Southampton Arts Center on Jobs Lane and quietly hosts some of the most museum-grade exhibitions on the East End. Past programs have featured Wolfgang Tillmans, Sanford Biggers, McArthur Binion, and a deep rotation of major contemporary voices.

• Rating: 4.9 stars (8 reviews)
• Address: 11 Jobs Lane, Southampton, NY 11968
• Why we love it: Small, focused, free admission, and the works on view are routinely museum-caliber

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The Galleries: Where Real Collecting Happens

The Hamptons gallery scene is concentrated in four villages, East Hampton, Sag Harbor, Southampton, and Bridgehampton, with smaller outposts in Wainscott and Water Mill. These are the spaces where summer programs change every few weeks and where the work that ends up in next year’s auction catalogs is first shown.

The White Room Gallery (East Hampton)

Repeatedly named one of the best galleries in the Hamptons, The White Room Gallery has anchored Main Street in East Hampton for over a decade. The 2026 summer slate is paced for return visits: IN THE FLOW (May 27 to June 28), TAKE OFF (July 1 to August 2), and GAME CHANGERS (August 4 to August 23). Co-curators Andrea McCafferty and Kat O’Neill are usually on-site and famously generous with their time.

A frequent visitor wrote, “A fun, comfortable atmosphere welcomes you at The White Room. The proprietors and curators are present, approachable, bright people who are immersed in the art world. Large space, lots of fun annexes.”

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Eric Firestone Gallery (East Hampton)

A heavyweight on Newtown Lane, Eric Firestone Gallery specializes in rediscovered post-war American art and ambitious historical group shows. The current exhibition, General, runs May 23 through June 28, 2026, and is typical of the program’s scholarship and reach.

• Rating: 5.0 stars (6 reviews)
• Address: 4 Newtown Lane, East Hampton, NY 11937
• Phone: (631) 604-2386

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A Three-Day Hamptons Art Itinerary

Here is how we suggest guests pace a long art weekend in summer 2026. The East End is bigger than it looks on a map; clustering by village keeps the driving manageable and leaves room for actual lunch.

Day 1, Water Mill and Southampton. Start with the Parrish Art Museum at opening at 11 AM. Lunch in Water Mill. Afternoon at Southampton Arts Center and the Peter Marino Art Foundation on Jobs Lane. Evening: a sunset dinner in Southampton village.

Day 2, East Hampton and Springs. Begin at Guild Hall, then walk Newtown Lane to Eric Firestone and Halsey McKay. Lunch in town. Afternoon drive to LongHouse Reserve for the sculpture gardens, then on to the Pollock-Krasner House in Springs by reservation.

Day 3, Sag Harbor and Bridgehampton. Morning at The Church, then Grenning Gallery and the Sag Harbor waterfront. Lunch on Main Street. Afternoon at Dia Bridgehampton and Tripoli Gallery in Wainscott. Optional dinner back in East Hampton.

If your stay overlaps July 9 to 12, swap one of these days for the Hamptons Fine Art Fair at the Southampton Fairgrounds and the satellite SculptureHamptons program at LongHouse.

Plan Your Hamptons Art Weekend with Us

The Hamptons in summer rewards travelers who plan around the art. Whether you are anchoring your stay around the Hamptons Fine Art Fair, building a slow itinerary across the museums, or chasing a specific opening at one of the galleries, this is one of the great American art weekends, hiding in plain sight at the eastern tip of Long Island.

When you are ready to plan, our team at Luxury Beach Getaway can help you choose the right home base and time your stay around the exhibitions and events that matter most to you. Browse our Hamptons vacation rentals or get in touch to design a summer art weekend that feels every bit as curated as the museums you are coming to see.

Frequently Asked Questions

When is the best month to experience the Hamptons art scene?
July is the peak month, anchored by the Hamptons Fine Art Fair from July 9 to 12, 2026, and overlapping with major openings at the Parrish, Guild Hall, LongHouse, and most leading galleries. August continues the momentum with a second wave of summer shows and the East Hampton Art Affair. June is quieter and well-suited to visitors who prefer to see the work without the gala-week energy.

Do I need to book tickets in advance for Hamptons museums?
Most institutions allow walk-ups, but tickets to the Hamptons Fine Art Fair Opening Night Vernissage, Pollock-Krasner House tours, and Watermill Center tours should be reserved in advance. Parrish Art Museum sells timed tickets online, which is the easiest way to avoid waiting on busy summer afternoons.

How many days do I need to see the Hamptons art scene properly?
Three days is the comfortable minimum to cover the major museums in Water Mill, East Hampton, and Sag Harbor along with two or three gallery walks. A long weekend overlapping the fair (July 9 to 12) can fold the fair, the SculptureHamptons satellite program, and one full museum day into the same trip.

Are Hamptons galleries free to enter?
Yes. All commercial galleries listed in this guide, including The White Room, Eric Firestone, Halsey McKay, Tripoli, and Grenning, are free to visit. Among museums and foundations, the Peter Marino Art Foundation and Dia Bridgehampton are free year-round, while the Parrish, Guild Hall, LongHouse, The Church, Southampton Arts Center, and Pollock-Krasner House charge modest admission.

What is the closest village to the most art venues?
East Hampton has the densest cluster of leading galleries on Newtown Lane plus Guild Hall and easy access to LongHouse Reserve and the Pollock-Krasner House. Southampton is the natural base for the Parrish (a short drive to Water Mill), the Southampton Arts Center, and the Peter Marino Art Foundation, and it is the host village for the Hamptons Fine Art Fair.

Is the Hamptons art scene only a summer thing?
Summer is the peak, but year-round institutions like Guild Hall, the Parrish, The Church, Southampton Arts Center, and Dia Bridgehampton mount exhibitions throughout the year. A September or early-October visit pairs lingering summer weather with full programming and noticeably smaller crowds.

The Hamptons and North Fork sit on one of the most densely planted, most carefully fished stretches of coastline in the country. Drive five miles in almost any direction out here and you will pass a working farm, a vineyard, a roadside stand, or a small fishing dock. That short distance, the radius between soil and plate, is the secret to the food we love most on the East End.

At Luxury Beach Getaway, we have spent close to twenty years helping guests settle into homes across the Hamptons and North Fork. We have eaten our way through every season, talked shop with chefs and farmers, and watched the same restaurant lift its menu three times in a single month because the corn finally came in, the fluke ran heavy, or the first heirloom tomatoes hit the stand. This guide is our take on farmstand to fine dining in the Hamptons: the chefs leading the movement, the farms feeding them, and how to taste the East End at its peak.

Why Five Miles Matters on the East End

The East End is a narrow ribbon of fertile land. On the South Fork, the Hamptons spread along a thin stretch of farmland between the Atlantic and Peconic Bay. On the North Fork, vineyards and produce fields run almost continuously from Riverhead to Orient Point. When a restaurant says it sources from a farm “down the road,” it usually means just that.

A few details that shape how chefs cook out here:

• The outdoor growing season is short and intense, roughly April through November, with a juicy peak from July to September.
• Many farms run their own stands, so chefs can shop the same shelves you do.
• The Peconic and Long Island Sound waters add year-round shellfish and a rotating cast of finfish to the picture.
• Long Island duck, local cheese, lavender, and small-batch preserves round out a deep bench of specialty foods.

The result is a tight, fast-moving food economy where a five-mile radius is not a marketing line. It is the supply chain.

Quick insight: Cornell Cooperative Extension of Suffolk County publishes a month-by-month harvest chart for local fruits and vegetables. East End chefs essentially treat that chart as their menu calendar.

Hamptons Chefs Building Menus Within Five Miles

The South Fork has a deep bench of chefs who treat the surrounding farms as an extension of their kitchen. Some have their own gardens. Others have decades-long handshake deals with the farmers a mile down the road. These are the restaurants we book ahead for when guests ask us where to eat something that feels truly of the Hamptons.

Nick & Toni’s

Nick & Toni’s in East Hampton is the godparent of the local farm-to-table scene. Behind the dining room sits a roughly one-acre organic garden, and the kitchen team harvests from it every day.

About thirty percent of the restaurant’s produce comes from that single plot, with the rest pulled from nearby South Fork farms. The wood-burning oven sets the rhythm of the menu, and dishes shift week to week as the garden and farms hand off whatever is at peak.

• Rating: 4.4 stars, 372 reviews
• Address: 136 N Main St, East Hampton, NY 11937
• Phone: 631-324-3550
• Hours: Dinner Wednesday through Monday, closed Tuesdays
• Try: the agnolotti pasta special or the daily market fish

Learn more about Nick & Toni’s

Topping Rose House

Topping Rose House in Bridgehampton brings high-end technique to East End ingredients. The restaurant is set inside a historic 1842 inn, with an on-site farm just a short walk away that supplies vegetables, eggs, and herbs throughout the season.

The menu reads like a love letter to the surrounding fields, with locally caught fish, Long Island duck, and produce that often traveled less than a mile from soil to plate.

• Rating: 4.3 stars, 408 reviews
• Address: 1 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932
• Phone: 631-808-2000
• Vibe: elegant inn dining, white tablecloths, ambitious cooking
• Try: anything with peak-season tomatoes or local duck

Learn more about Topping Rose House

Almond

Almond, in the heart of Bridgehampton, is chef Jason Weiner’s neighborhood bistro and a quiet champion of South Fork producers. The menu names its farms and fishermen, and the team works closely with the people pulling food out of the ground and the water that same week.

Expect a relaxed bistro feel, attentive servers, and dishes that read simple but taste deeply seasonal.

• Rating: 4.4 stars, 312 reviews
• Address: 1 Ocean Rd, Bridgehampton, NY 11932
• Phone: 631-537-5665
• Hours: Dinner Tuesday through Saturday, closed Sunday and Monday
• Try: hanger steak frites, the daily market fish

Learn more about Almond

Highway Restaurant and Bar

Highway sits on Montauk Highway just east of East Hampton village, and chef Joe Isidori’s kitchen leans hard into East End seafood and produce. T

he room is warm and easy, the bar pours thoughtful cocktails, and the menu turns over with the seasons. We send guests here when they want an East End dinner without the formality of the bigger-ticket dining rooms.

• Rating: 4.3 stars, 172 reviews
• Address: 290 Montauk Hwy, East Hampton, NY 11937
• Phone: 631-527-5372
• Vibe: lively, contemporary American, strong cocktail program
• Try: the daily frittata at brunch, market fish at dinner

Learn more about Highway Restaurant and Bar

Local tip: If you are based on the South Fork and want to taste a chef’s tightest local sourcing, ask the host which dishes are featuring ingredients from a specific farm that week. The team will usually steer you straight to whatever just came in.
If you are planning a Hamptons food trip, our Hamptons vacation rentals put you within minutes of every kitchen above.

North Fork Chefs Working the Tightest Radius on Long Island

The North Fork is one of the most concentrated farm-to-table corridors in the country. From Riverhead to Orient Point, restaurants sit within easy walking distance of working farms, oyster floats, and small commercial docks. Many chefs out here shop the same farmstands their guests do, often on the morning of service.

If you are planning a North Fork weekend, our North Fork vacation rentals put you within minutes of every spot below.

North Fork Table and Inn

North Fork Table and Inn in Southold has long been treated as the reference point for fine dining on the North Fork. The restaurant sits in the middle of Southold’s farming district, surrounded by vineyards and produce farms, and the kitchen leans on those neighbors for nearly everything that lands on the plate.

The tasting and prix-fixe menus rotate with the harvest and reflect the deep relationships the team has built with East End growers and fishermen.

• Rating: 4.5 stars, 396 reviews
• Address: 57225 Main Rd, Southold, NY 11971
• Phone: 631-765-0177
• Vibe: refined, white-tablecloth, ambitious tasting menus
• Try: the seasonal prix fixe, especially in late summer

Learn more about North Fork Table and Inn

Bruce and Son

Bruce and Son in Greenport is where we send guests for a slow, vegetable-forward brunch that reads like a farm tour on a plate. Chef Bruce Miller leans on North Fork farms for nearly everything in the kitchen, and the daily menu shifts with what is fresh that morning.

The summer succotash is the kind of dish that only works when the corn, beans, and tomatoes all peak at once.

• Rating: 4.4 stars, 344 reviews
• Address: 208 Main St, Greenport, NY 11944
• Hours: 9 AM to 2:30 PM, closed Tuesday and Wednesday
• Vibe: sunny, casual, very Greenport
• Try: the BLT with sugar bacon, summer succotash

Learn more about Bruce and Son

8 Hands Farm

8 Hands Farm in Cutchogue is one of the clearest examples of a true farm kitchen on the North Fork. The family raises pigs and sheep, grows organic vegetables, and runs a small farm store and prepared foods program right on the property. The menu changes constantly because everything on it came out of those barns or fields a few hundred feet away. Periodic farm dinners turn the property into one of the most direct farm-to-fork experiences on Long Island.

• Rating: 4.7 stars, 168 reviews
• Address: 4735 Cox Ln, Cutchogue, NY 11935
• Phone: 631-494-6155
• Hours: Thursday through Sunday only
• Try: pasture-raised eggs, fresh baked goods, frozen custard

Learn more about 8 Hands Farm

How Chefs Map the East End Growing Calendar

Every chef we talk to out here keeps a loose seasonal framework and then lets the farms write the details. Here is the rhythm to expect across a typical year.

Spring (April to May)

The first menus of the season lean light and green. Look for:

• Asparagus, lettuces, radishes, scallions, rhubarb
• North Fork specialties like Hakurei turnips and young garlic
• Lighter fish preparations as fluke and striped bass return

Early Summer (June)

June is the strawberry and pea window. Restaurants pivot dessert programs almost overnight, and the brief sour cherry harvest at farms like Wickham’s drives quietly excited specials at the more serious kitchens.

High Summer (July to August)

This is when the menu almost writes itself. Tomatoes, sweet corn, summer squash, peaches, melons, and stone fruit hit at once. Chefs lean into raw and barely cooked plates, crudo, succotash, and grilled local fish over peak vegetables.

Late Summer to Fall (September to October)

The hand-off from summer to fall is the most exciting window for a food-focused trip. Tomatoes still hang on while apples, grapes, squash, and pumpkins come in. Long Island duck pairs with late stone fruit, and many restaurants host harvest dinners with their farm partners.

Late Fall and Winter (November to March)

Outdoor harvest narrows, but the kitchens stay interesting. Peconic Bay scallops, in years when the fishery is open, become the marquee winter ingredient. Storage crops, brassicas, and house-preserved summer produce keep menus rooted in place.

Did you know: Peconic Bay scallop season traditionally opens on the first Monday in November. When the harvest is strong, top East End kitchens build entire menus around the brief window.

Tips for Eating the Five-Mile Hamptons

• Book ahead in season. From Memorial Day through Columbus Day, the most farm-driven restaurants fill up two to four weeks out, especially on Friday and Saturday nights.
• Ask your server about the farm. Most East End kitchens are happy to tell you exactly which farm or dock supplied a dish that day, and the answer often shapes the next decision on the menu.
• Shop the stands before dinner. A morning at Balsam, Amber Waves, or Wickham’s helps you read the menu more clearly later that night.
• Pair with the wineries. A bottle of local rosé or a North Fork red turns a casual farmstand meal at the house into a full East End experience.
• Plan around the harvest. Late July through September is peak, but late September and October are quieter, gorgeous, and arguably the best time for food-focused trips.

Taste the East End With Us

The Hamptons and North Fork reward travelers who slow down, follow the harvest, and let the chefs out here do what they do best. From farmstand sweet corn at midday to a tasting menu built on Peconic Bay scallops at night, the food on the East End is genuinely tied to the land and water you can see from the window of your rental.

At Luxury Beach Getaway, we love helping guests plan stays that lean into this kind of eating. Tell us when you would like to visit and what you would like to taste, and we will help you find a home, a route through the farms and restaurants, and a few quiet places to sit with a glass of local wine at the end of the day. Browse our East End vacation rentals to start planning, or reach out to our team for help.

Frequently Asked Questions

What does farm-to-table actually mean on the East End?
On the East End, farm-to-table is unusually literal. Many restaurants source vegetables, fruit, eggs, dairy, fish, and shellfish from named farms and docks within a short drive, and several have their own gardens or farms on the same property.

Which Hamptons restaurant has its own garden?
Nick & Toni’s in East Hampton is the best known example, with a roughly one-acre organic garden behind the dining room. Estia’s Little Kitchen in Sag Harbor and Topping Rose House in Bridgehampton also grow produce on their own properties.

Where can travelers shop the same farmstands the chefs use?
Balsam Farm in Amagansett, Amber Waves in Amagansett, and Wickham’s in Cutchogue are all open to the public and supply some of the most respected restaurants on the East End. Many other small stands operate seasonally along Route 27 on the South Fork and Route 25 on the North Fork.

What is the best time of year to visit for farm-to-table dining?
Late July through early October is the peak window, with the widest variety of local produce and seafood. September and early October offer slightly smaller crowds, cooler evenings, and the addition of fall fruits, squash, and apples.

Do farm-to-table restaurants stay open year round?
Many do, though some run shorter winter hours or close midweek. Peconic Bay scallop season starts in November and gives serious restaurants a strong reason to keep cooking through the colder months.

Can travelers attend a farm dinner during their stay?
Yes, often. Properties like Amber Waves Farm in Amagansett and 8 Hands Farm in Cutchogue host periodic chef collaboration dinners during the season, and wineries like Wölffer Estate run wine and food events. These sell out quickly, so it pays to plan ahead.

The US Open Golf 2026 comes home to our backyard this June, and we could not be more excited. From June 18 through June 21, 2026, the 126th U.S. Open Championship returns to Shinnecock Hills Golf Club in Southampton, the sixth time this historic links has hosted the biggest tournament in American golf.

At Luxury Beach Getaway, we have spent nearly twenty years helping guests experience the best of the Hamptons and the North Fork. We know the back roads, the quiet beaches, the dinner reservations that book up first, and yes, the shortest routes to the course. This is our local guide to making the most of US Open week, whether you have tickets in hand or simply want to be part of the energy.

Here is what we cover: the key dates and ticket details, what makes Shinnecock so special, where to eat and stay nearby, and how to plan a week that pairs world-class golf with the unhurried luxury our region is known for.

The 2026 US Open at a Glance

The championship runs from Thursday, June 18 to Sunday, June 21, 2026, with practice rounds and pre-tournament activities beginning Monday, June 15. The merchandise pavilion opens to the public from June 11 through June 14, no ticket required, with parking at Stony Brook Southampton.

Spectators driving in from the east will park at the Hampton Classic Horse Show grounds in Bridgehampton and ride shuttles to the course. Tickets range from gallery passes for the early practice days to premium hospitality packages in the Trophy Club and the exclusive 1895 Club, all available through the USGA’s official channels.

This will be the 6th U.S. Open hosted at Shinnecock and its 10th overall USGA championship, a reflection of just how central this course is to the history of American golf.

The Venue: Shinnecock Hills Golf Club

Shinnecock Hills Golf Club

Founded in 1891, Shinnecock Hills is one of the five founding clubs of the USGA and the oldest incorporated golf club in the country. The course you will see on television is the William Flynn 1931 routing, a windswept, sandy, links-style layout that sits between the Atlantic Ocean and Peconic Bay. It is a course famous for asking every kind of question of every kind of golfer, often within a single hole.

Past champions here read like a hall of fame: Raymond Floyd (1986), Corey Pavin (1995), Retief Goosen (2004), and Brooks Koepka (2018). 2026 marks the 6th U.S. Open at the club, and locals will tell you the firm fairways and unrelenting wind off the bay are part of the show.

• Rating: 4.5 stars (394 reviews)
• Address: 200 Tuckahoe Rd, Southampton, NY 11968
• Phone: (631) 283-1310
• Website: shinnecockhillsgolfclub.org
• What to expect: Links-style par 70, exposed to coastal wind, historically firm and fast

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Hampton Classic Horse Show Grounds (Shuttle Parking)

If you are coming from the east, this is where your week begins. The Hampton Classic grounds in Bridgehampton serve as the official spectator parking lot, with shuttles running to and from the course throughout the day. Plan to arrive early, especially on weekend rounds, and pack lightweight layers because the morning fog off the bay can take a while to burn off.

• Rating: 4.7 stars (269 reviews)
• Address: 240 Snake Hollow Rd, Bridgehampton, NY 11932
• Tip: Bring a clear bag that meets USGA size requirements; security lines move fastest before 7 a.m.

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Where to Eat Near Shinnecock Hills

Dinner reservations during US Open week are gold. We recommend booking your top picks two to four weeks ahead, especially anything Thursday through Sunday. Here are our favorites, sorted from closest to the course outward.

Sant Ambroeus Southampton

A Milanese institution on Main Street, Sant Ambroeus is our pick for an elegant lunch between rounds or a polished dinner after. Strong espresso, beautiful pastries in the morning, and a pasta menu that does not disappoint. It is the kind of place where you settle in and let the day slow down.

• Rating: 4.4 stars (555 reviews)
• Address: 30 Main St, Southampton, NY 11968
• Phone: (631) 283-1233
• Best for: Breakfast pastries, espresso, weekend brunch, refined dinner

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Tutto Il Giorno

Chic modern Italian with a leafy outdoor patio that feels miles away from Main Street even though it is just around the corner. Tutto Il Giorno is consistent, the wine list is thoughtful, and the calm vibe is a welcome counterweight to a day in the sun. Book ahead.

• Rating: 4.3 stars (335 reviews)
• Address: 56 Nugent St, Southampton, NY 11968
• Phone: (631) 377-3611
• Best for: Date-night dinner, garden seating, pasta and seafood

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75 Main

A Southampton classic that runs all day and gets lively into the evening. 75 Main is our go-to when guests want a buzzy, casual dinner with a wide menu and the option to spill out onto the sidewalk. Late-night crowds can build, so an earlier reservation is the move.

• Rating: 4.2 stars (1,175 reviews)
• Address: 75 Main St, Southampton, NY 11968
• Phone: (631) 283-7575
• Best for: Casual but lively dinners, people-watching, group reservations

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Le Charlot

A small French bistro tucked just off Main Street with a friendly bar and an honest menu of classics. Le Charlot is where we send guests who want steak frites, a glass of Bordeaux, and a room that feels like Paris in the summer.

• Rating: 3.8 stars (182 reviews)
• Address: 36 Main St, Southampton, NY 11968
• Phone: (631) 353-3222
• Best for: French bistro classics, late dinner, lively bar

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Beaches Worth a Detour During US Open Week

The course will run early; afternoons are when the Hamptons coastline calls. These are our favorites within a short drive of Shinnecock.

Cooper’s Beach (Southampton)

Routinely named one of the best beaches in America, Cooper’s Beach is the wide, white-sand crown jewel of Southampton Village. Lifeguards, restrooms, a snack bar, and chair rentals make it easy. Plan to pay a daily non-resident parking fee and arrive before mid-morning on weekend days.

• Rating: 4.7 stars (1,607 reviews)
• Address: 268 Meadow Ln, Southampton, NY 11968
• Best for: Classic ocean beach day, family-friendly amenities, sunset walks

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Ponquogue Beach (Hampton Bays)

A long, scenic ocean beach on a barrier island just west of the course. Ponquogue is often less crowded than Cooper’s and is one of our favorites for a peaceful late-afternoon swim after a long day on the grounds. Day passes are typically easier to come by here.

• Rating: 4.7 stars (697 reviews)
• Address: 280 Dune Rd, Hampton Bays, NY 11946
• Best for: A quieter ocean day, surf, long walks

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Vineyards and Off-Course Experiences

When the leaderboard goes quiet, the East End opens up. Wine country is a 30-minute drive from Shinnecock, and the village energy across the South Fork is at its summer peak.

Wölffer Estate Vineyard (Sagaponack)

A short drive from the course, Wölffer Estate is the most recognizable wine destination on the South Fork. Beautiful grounds, the famous Summer in a Bottle rosé, and the wine stand at the back of the property is one of our favorite easy-going afternoon stops. They host live music many evenings during the summer.

• Rating: 4.3 stars (707 reviews)
• Address: 139 Sagg Rd, Sagaponack, NY 11962
• Phone: (631) 537-5106
• Best for: Rosé tastings, lawn picnics, sunset wine stand

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Channing Daughters Winery (Bridgehampton)

A boutique winery just a couple of miles from the parking shuttle lot, Channing Daughters is known for inventive small-batch wines and a sculpture-filled tasting garden. Quieter than the better-known names, which is exactly why we love sending guests here.

• Rating: 4.6 stars (201 reviews)
• Address: 1927 Scuttle Hole Rd, Bridgehampton, NY 11932
• Phone: (631) 537-7224
• Best for: Small-batch tastings, garden visits, low-key wine afternoons

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Agawam Park (Southampton Village)

A pretty, lakeside village park right in downtown Southampton. Agawam Park is the quiet between-rounds spot, with shaded paths, a playground, and summer concerts on the lawn. It is also a great place to stretch your legs after a day at the course.

• Rating: 4.7 stars (143 reviews)
• Address: 51 Pond Ln, Southampton, NY 11968
• Best for: Quiet walk, family stop, free summer concerts

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Sag Harbor Village

Spend an afternoon walking Sag Harbor: the old whaling village turned bookstore-and-boutique town, with a working harbor and some of the best people-watching on the East End. Grab a coffee, browse the shops on Main Street, and stay for a harborfront dinner.

• Location: Sag Harbor, NY 11963
• Best for: Village walk, independent shops, harbor views

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Our Local Tips for US Open Week 2026

After two decades of hosting guests for events like this one, here is the practical advice we share most often.

• Book everything early. Dinner reservations, tee times at other public courses, and especially your stay. The week of June 18 to 21, 2026, will be the busiest week of the year in Southampton.
• Plan around the shuttle. If you are staying east of Shinnecock (Bridgehampton, Sag Harbor, East Hampton), you will use the Hampton Classic shuttle lot. Build that into your morning timing.
• Pack for the weather. June on the East End can swing from cool, foggy mornings to bright, breezy 80s by mid-day. Layers, sunscreen, and a hat are non-negotiable.
• Pre-buy a clear bag that meets USGA size limits. It saves time at security and is one of the most overlooked details.
• Schedule a “no-golf” day. Even die-hard fans burn out. Plan one beach morning or a vineyard afternoon in the middle of the week. You will enjoy the championship rounds more for it.
• Use the merchandise pavilion smartly. Pre-championship days (June 11 to 14) let you shop without needing a tournament ticket, with parking at Stony Brook Southampton.
• Lock in transportation. Car services and rideshares get strained mid-week. If you can, rent a car ahead of time.

Plan Your 2026 US Open Trip With Us

The 2026 US Open at Shinnecock Hills is going to be one of the most memorable weeks the Hamptons has seen in years. Whether you are coming for one round or staying the entire week, the difference between a good trip and a great one usually comes down to where you stay, who is helping you plan it, and how well you know the area.

At Luxury Beach Getaway, we have built our business on local knowledge and hands-on service. If you are ready to lock in your stay for US Open Golf 2026, browse our US Open Collection or reach out to our team. We will help you find the right home, share our favorite spots, and make sure your week feels effortless from arrival to checkout.

Frequently Asked Questions

How many times has Shinnecock Hills hosted the US Open?
2026 will be the sixth U.S. Open at Shinnecock Hills. Previous Opens at the club were held in 1896, 1986, 1995, 2004, and 2018, with champions including Raymond Floyd, Corey Pavin, Retief Goosen, and Brooks Koepka.

Where do US Open spectators park?
Spectators driving in from the east will park at the Hampton Classic Horse Show grounds in Bridgehampton (240 Snake Hollow Rd) and take official shuttles to the course. Pre-tournament merchandise shopping uses parking at Stony Brook Southampton. Always check the latest USGA fan guide for current details.

What should I bring to the US Open at Shinnecock?
Plan for a long day outdoors: sunscreen, a hat, comfortable walking shoes, a clear bag that meets USGA size requirements, a refillable water bottle, and layered clothing for the morning fog and afternoon heat. Cell coverage on the course can be uneven, so download your tickets ahead of time.

How early should I book a Hamptons vacation rental for US Open week?
For the 2026 US Open we recommend booking as far in advance as possible, ideally 6 to 9 months ahead. The best homes near Southampton, Water Mill, and Bridgehampton are typically the first to go, and pricing favors early reservations.